Highland Square Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
Berrodin Bed & Breakfast
814 Bloomfield Ave Akron OH
Stay at this B&B in Akron. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Highland Theater and Dr. Bob's Home are located nearby.
La Quinta Inn & Suites by Wyndham Cleveland Macedonia
268 East Highland Rd Macedonia OH
Book a stay at this business-friendly hotel in Macedonia. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Kent State University Hotel and Conference Center
215 S. Depeyster Street Kent OH
Book a stay at this business-friendly hotel in Kent. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean ...
The Aurora - a Boutique Hotel
30 Shawnee Trail Aurora OH
Book a stay at this business-friendly hotel in Aurora. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
Comfort Inn & Suites Cuyahoga Falls - Akron
1420 Main St Cuyahoga Falls OH
Book a stay at this business-friendly hotel in Cuyahoga Falls. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Royal Inn & Suites
2677 Gilchrist Rd Akron OH
Book a stay at this business-friendly hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Courtyard by Marriott Canton
4375 Metro Cir Nw Canton OH
Book a stay at this business-friendly hotel in Canton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Quality Inn & Suites Medina - Akron West
2850 Medina Road Medina OH
Book a stay at this business-friendly hotel in Medina. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Comfort Inn & Suites Akron South
1025 Interstate Pkwy Akron OH
Book a stay at this business-friendly hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Courtyard by Marriott Akron Stow
4047 Bridgewater Pkwy Stow OH
Book a stay at this business-friendly hotel in Stow. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff ...
Spark by Hilton Akron Fairlawn
4073 Medina Road Akron OH
Book a stay at this business-friendly hotel in Akron. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. ...
Comfort Inn Hall of Fame
5345 Broadmoor Cir Nw Canton OH
Book a stay at this business-friendly hotel in Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hyatt Place Canton
5421 Whipple Ave NW North Canton OH
Book a stay at this business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Plus North Canton Inn & Suites
6889 Sunset Strip Avenue NW North Canton OH
Book a stay at this business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Baymont by Wyndham Copley Akron
130 Montrose West Ave Akron OH
Book a stay at this business-friendly hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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View all propertiesLowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Sep 14 - Mon, Sep 21
MCO
Orlando Intl.
CLE
Hopkins Intl.
$98
Roundtrip
found 5 days ago
Wed, Oct 21 - Tue, Oct 27
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$119
Roundtrip
found 1 day ago
Wed, Oct 21 - Tue, Oct 27
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$151
Roundtrip
found 1 day ago
Mon, Sep 14 - Thu, Sep 24
MCO
Orlando Intl.
CAK
Akron-Canton
$162
Roundtrip
found 3 days ago
Wed, Sep 23 - Sat, Sep 26
MCO
Orlando Intl.
CLE
Hopkins Intl.
$277
Roundtrip
found 6 hours ago
Best points of interest in Akron
- Dr. Bob's Home Vacations
- Highland Theater Vacations
- Coach House Theater Vacations
- Cuyahoga Valley National Park Vacations
- Blossom Music Center Vacations
- University of Akron Vacations
- Belden Village Mall Vacations
- MGM Northfield Park Vacations
- Gervasi Vinyard & Italian Bistro Vacations
- Kent State University Vacations
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